Catalytic amination of benzyl alcohol using ruthenium cymene compounds containing bidentate N,O-donor ancillary ligands

A new class of half-sandwich (η 6 -p-cymene) ruthenium(II) complexes supported by 2-aminofluorene derivatives [Ru(η 6 -p-cymene)(Cl)(L)] (L = 2-(((9H-fluoren-2-yl)imino)methyl)phenol (L 1 ), 2-(((9H-fluoren-2-yl)imino) methyl)-3-methoxyphenol (L 2 ), 1-(((9H-fluoren-2-yl)imino)methyl)naphthalene-2-ol (L 3 ) and N-((1H-pyrrol-2-yl)methylene)-9H-fluorene-2-amine (L 4 )) were synthesized. All compounds were fully characterized by analytical and spectroscopic techniques (IR, UV-Vis, NMR) and also by mass spectrometry. The solid state molecular structures of the complexes [Ru(η 6 -p-cymene)(Cl) (L 2 )], [Ru(η 6 -p-cymene)(Cl)(L 3 )] and [Ru(η 6 -p-cymene)(Cl)(L 4 )] revealed that the 2-aminofluorene and p-cymene moieties coordinate to ruthenium(II) in a three-legged piano-stool geometry. The synthesized complexes were used as catalysts for the dehydrogenative coupling of benzyl alcohol with a range of amines (aliphatic, aromatic and heterocyclic). The reactions were carried out under thermal heating, ultrasound and microwave assistance, using solvent or solvent free conditions, and the catalytic performance was optimized regarding the solvent, the type of base, the catalyst loading and the temperature. Moderately high to very high isolated yields were obtained using [Ru(η 6 -pcymene)(Cl)(L 4 )] at 1 mol%. In general, microwave irradiation produced better yields than the other two techniques irrespective of the nature of the substituents.

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Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η⁶‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Vinoth

Indira

Bharathi

et al. 2019

Applied Organom Chemis

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Aerobic activation of alcohols on Zn-promoted atomically-dispersed Ru sites encapsulated within UiO-66 framework for imine synthesis

Shang

Zhang

Lin

et al. 2022

Applied Catalysis B: Environmental

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Ruthenium catalyzed amination cyclization of 1,2,4-butanetriol with primary amines: A borrowing hydrogen strategy for 3-pyrrolidinol synthesis

et al. 2020

Chinese Chemical Letters

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Catalytic amination of benzyl alcohol using ruthenium cymene compounds containing bidentate N,O-donor ancillary ligands

Cited by 5 publications

References 49 publications

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η⁶‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η⁶‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Aerobic activation of alcohols on Zn-promoted atomically-dispersed Ru sites encapsulated within UiO-66 framework for imine synthesis

Ruthenium catalyzed amination cyclization of 1,2,4-butanetriol with primary amines: A borrowing hydrogen strategy for 3-pyrrolidinol synthesis

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Catalytic amination of benzyl alcohol using ruthenium cymene compounds containing bidentate N,O-donor ancillary ligands

Cited by 5 publications

References 49 publications

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η6‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η6‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Aerobic activation of alcohols on Zn-promoted atomically-dispersed Ru sites encapsulated within UiO-66 framework for imine synthesis

Ruthenium catalyzed amination cyclization of 1,2,4-butanetriol with primary amines: A borrowing hydrogen strategy for 3-pyrrolidinol synthesis

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Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η⁶‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives

Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half‐Sandwich (η⁶‐p‐cymene) Ruthenium(II) Complexes Stabilised by 2‐aminofluorene Derivatives